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Yiqing Feng, Max M. Majireck and Prof. Dr. Steven M. Weinreb Total Synthesis of the Unusual Monoterpenoid Indole Alkaloid (±)-Alstilobanine A Angewandte Chemie International Edition 51

Article first published online: 19 NOV 2012 | DOI: 10.1002/anie.201207949

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Tetracyclic monoterpene alkaloid alstilobanine A was obtained in racemic form. The pivotal steps of the total synthesis are a novel conjugate addition of an ester enolate with a nitrosoalkene, as well as a formal [2+2] intramolecular cycloaddition leading to a β-lactone to generate the requisite cis-fused 2-azadecalin moiety of the alkaloid. TMSE=trimethylsilylethoxy, Ts=4-toluenesulfonyl.

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